CN1776535B - Toner preparation process - Google Patents
Toner preparation process Download PDFInfo
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- CN1776535B CN1776535B CN200510124759.1A CN200510124759A CN1776535B CN 1776535 B CN1776535 B CN 1776535B CN 200510124759 A CN200510124759 A CN 200510124759A CN 1776535 B CN1776535 B CN 1776535B
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08706—Polymers of alkenyl-aromatic compounds
- G03G9/08708—Copolymers of styrene
- G03G9/08711—Copolymers of styrene with esters of acrylic or methacrylic acid
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
- G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08706—Polymers of alkenyl-aromatic compounds
- G03G9/08708—Copolymers of styrene
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08713—Polyvinylhalogenides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08713—Polyvinylhalogenides
- G03G9/08715—Polyvinylhalogenides containing chlorine, bromine or iodine
- G03G9/08717—Polyvinylchloride
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08722—Polyvinylalcohols; Polyallylalcohols; Polyvinylethers; Polyvinylaldehydes; Polyvinylketones; Polyvinylketals
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08724—Polyvinylesters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08726—Polymers of unsaturated acids or derivatives thereof
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08726—Polymers of unsaturated acids or derivatives thereof
- G03G9/08733—Polymers of unsaturated polycarboxylic acids
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08791—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by the presence of specified groups or side chains
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08795—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08784—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775
- G03G9/08797—Macromolecular material not specially provided for in a single one of groups G03G9/08702 - G03G9/08775 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/09775—Organic compounds containing atoms other than carbon, hydrogen or oxygen
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Developing Agents For Electrophotography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present disclosure relates to a toner preparing process including a first heating of a latomer mixture including at least one free radical polymerizable monomer, and at least one alkylene anhydride; a second heating of the latomer mixture to form polymeric particles; and combining the polymeric particles with at least one amine.
Description
Technical field
The disclosure relates to toner and application and preparation method.
background technology
In known resin application, polymkeric substance used often comprises containing acrylic monomers.Then this base polymer can be assembled by for example polyaluminium chloride (PAC) method.But, may be difficult to participate in stable radical polymerization process containing acrylic monomers, as being combined with styrene.The disclosure is described the method that free radical polymerisation process that a kind of use is stable is prepared latex, and the latex obtaining thus can assemble and be condensed into toner-particle subsequently.
summary of the invention
In disclosed several respects, a kind of method is provided, the method comprises that heat packs is containing the latex mixture of at least one free radical polymerizable monomer and at least one alkene class acid anhydrides for the first time; Heat for the second time this latex mixture to form polymer beads; And combine at least one amine and this polymer beads, wherein for the second time heating-up temperature higher than heating-up temperature for the first time; A kind of method for manufacturing toner, the method comprises provides the resin that comprises polymer beads microemulsion, described polymer beads to comprise at least one free radical polymerizable monomer compound and at least one alkene class acid anhydrides; This microemulsion of blend and at least one colorant, at least one amine and at least one optional wax; Lower than or approximate under resin emulsion glass transition temperature (Tg) heating gained potpourri; Higher than or approximate under resin emulsion glass transition temperature (Tg) heating gained potpourri; And a kind of latex preparation method, the method comprise heat packs for the first time containing the latex mixture of at least one free radical polymerizable monomer to low-conversion, then add at least one alkene class acid anhydrides; Heat for the second time this latex mixture to low-conversion; Heat for the third time this latex mixture to form polymer beads; And combine at least one amine and this polymer beads.In addition, other side of the present disclosure also relates to the toner product being obtained by method as herein described.
embodiment
Disclosed method can be used to the latex that toner-particle can be assembled and be condensed into preparation.
The disclosure is described a kind of method of preparing latex, and the method comprises that heat packs is containing the latex mixture of at least one free radical polymerizable monomer and at least one alkene class acid anhydrides for the first time; Heat for the second time this latex mixture to form polymer beads; And combine at least one amine and this polymer beads.
The heating for the first time of the first potpourri can, at for example approximately 50 ℃~approximately 145 ℃, more particularly for example be carried out for example approximately 5 minutes~approximately 4 hours more particularly approximately 20 minutes~approximately 1 hour under the polymerization temperature of approximately 120 ℃~approximately 130 ℃.Heating condition can become according to for example reaction scale and desired result.
Described at least one free radical polymerizable monomer can comprise a functional group and can be selected from following known free radical polymerizable monomer, for example unsaturated monomer, if styrene monomer (as styrene sulfonic acid, 4-vinyl benzoic acid), conjugated compound, 9-vinylcarbazole compound, vinyl chloride compound, vinyl acetate ester compounds, acrylic monomers and general formula thereof are (CH
2=CH) derivant of COOR-COOH (wherein R base can be an aliphatic interval base, for example to give different water wettabilities), as butyl acrylate, ethyl acrylate, hydroxy-ethyl acrylate; Methacrylate and general formula thereof are (CH
2=CCH
3) derivant of COORCOOH (wherein R base can be an aliphatic interval base, for example to give different water wettabilities), as methyl methacrylate, butyl methacrylate, etc.; And their potpourri.With respect at least one alkene class acid anhydrides, the amount of described at least one free radical polymerizable monomer in latex mixture can be for example approximately 85 % by weight~approximately 99 % by weight.
Described at least one free radical polymerizable monomer can with at least one alkene class acid anhydrides copolymerization.For example, at least one free radical polymerizable monomer, as styrene, can with the ratio copolymerization of for example maleic anhydride (MA) with 1: 1.In embodiments, copolymerization can generate the polymkeric substance that general formula is (A-B) n, and wherein A is that at least one stable free radical polymerizable monomer and B are at least one alkene class acid anhydrides.In the time that the amount of described at least one free radical polymerizable monomer in the first potpourri exceedes at least one alkene class acid anhydrides, think that polymerization can be performed until at least one alkene class acid anhydrides and all exhaust, then remaining at least one free radical polymerizable monomer continues polymerization.In embodiments, the first potpourri can contain three base polymers, for example poly-(styrene/MA), poly-(styrene/MA-block-styrene) segmented copolymer and polystyrene.
Described at least one alkene class acid anhydrides can be any acid anhydrides of the two keys of band, if this acid anhydrides can with at least one free radical polymerizable monomer polymerization.The non-limiting example of at least one alkene class acid anhydrides comprises maleic anhydride, 2,3-dialkyl group maleic anhydride is as 2,3-dimethyl maleic anhydride, 2,3-diphenyl maleic anhydride, tetrabydrophthalic anhydride, n-methylisatin acid anhydrides etc., and their potpourri.In latex mixture, latex refers to for example latex mixture, each component (for example monomer and alkene class acid anhydrides) can be one type or formed above by two classes or two classes.With respect at least one free radical polymerizable monomer, the amount of described at least one alkene class acid anhydrides in latex mixture is for example approximately 0.1 % by weight~approximately 20 % by weight.
In embodiments, for carrying out bulk polymerization or the solution polymerization of at least one free radical polymerizable monomer and at least one alkene class acid anhydrides, select the component of latex mixture and the heating condition of latex mixture.
Latex mixture also can comprise at least one radical initiator, this initiating agent can be selected from superoxide and two azo compounds, as benzoyl peroxide, di-t-butyl peroxide, 4, 4 '-azo, two valeronitriles and 4, 4 '-azo two (cyano group hexane), hydrogen peroxide, t-butyl hydroperoxide, 2, 2 '-azo two (2-amidine propane) dihydrochloride, 2, 2 '-azo two (2-methyl-prop amidine) dihydrochloride, 4, 4 '-azo two (4-cyanopentanoic acid), 4, 4 '-azo two (4-cyanopentanoic acid), potassium persulfate and amino persulfate.Described at least one radical initiator can be dissolved in immiscible liquids.With respect at least one free radical polymerizable monomer, the amount of described at least one radical initiator can be for example approximately 0.01 % by weight~approximately 5 % by weight, more particularly for example approximately 1 % by weight~approximately 3 % by weight.
Latex mixture dispersibles in the immiscible liquids that contains at least one surfactant.Described immiscible liquids can be any aqueous solution or potpourri, and for example water, as long as contained monomer or pre-polymerization resin in the insoluble solution latex mixture of this liquid.
Described at least one surfactivity can be selected from negative ion conventional in emulsion polymerization, kation, zwitter-ion and non-ionic surfactant.In embodiments, described at least one surfactant can be ionic surface active agent, the higher temperature that this class surfactant generally can be more suitable for relating in this method.The non-limiting example of anionic surfactant comprises alkyl aryl sulfonate, alkylsurfuric acid alkali metal salt, sulfonated alkyl ester, fatty acid soaps, etc., as alpha-olefin (C
14-C
16) sodium sulfonate.The example of surfactant is alkyl aryl sulphonic acid alkali metal salt.In embodiments, applicable anionic surfactant comprises alkyl sulfonate or alkylaryl sulfonate, for example pelopon A (" SDBS ").The suitable stabilization compound that can be used for the inventive method is found in " McCutcheon ' s Emulsifiers and Detergents 1981 Annual " book as the inventory of surfactant.
The consumption of described at least one surfactant can change, as long as obtain satisfied microemulsion for example to exceed critical micelle concentration (CMC).Based on the weight of immiscible liquids, the amount of described at least one surfactant can be for example approximately 1 % by weight~approximately 10 % by weight, for example approximately 2 % by weight~approximately 5 % by weight, and for example approximately 2 % by weight~approximately 3 % by weight.
Optionally can add at least one stabilizing agent further to reduce because of the caused diffusion of Oswald maturation.Described at least one stabilizing agent can be water-soluble low compound, also can be substantially water-fast, for example, containing approximately 10~approximately 40 carbon atoms, the for example long chain hydrocarbon of approximately 15~approximately 25 carbon atoms, alcohol, mercaptan, carboxylic acid, ketone, amine, hydrocarbon or any other long chain molecule, no matter with or without the functional group of interference stability free radical or microemulsion chemistry not substantially, for example lauryl mercaptan, hexadecane, cetyl alcohol, etc., and their potpourri.The mol ratio of described at least one stabilizing agent and monomer can be approximately 0.004~approximately 0.08, for example approximately 0.005~approximately 0.05.The mol ratio of described at least one stabilizing agent and at least one stabilization compound can be approximately 0.1~approximately 10, for example approximately 0.5~approximately 5.
Then, the latex mixture of this dispersion can be formed to microemulsion under high shear forces.In embodiments, term " microemulsion " refers to that diameter is less than approximately 1.5 μ m, and for example diameter is less than the aqueous dispersion of metastable hydrophobic of approximately 1 μ m.Shear action can realize by various high shear mixing equipment, for example, and piston type homogenizer, Micro Fluid bed, polytron, ultrasonication machine, static mixer and similar devices.In embodiments, microemulsion can be approximately 1,000~approximately 30 in piston type homogenizer for example, 000psi, and for example approximately 5,000~approximately 20, under 000psi pressure, in approximately 1~60 minute, for example, within approximately 5~approximately 45 minutes, form.Shear action may be defined as particle size is decreased to the acting force that nanoscale applies from micron order.
Any moment before forming polymer beads can add many other components in microemulsion, as at least one radical initiator.In embodiments, at least one other component can be added latex mixture before shearing.In other embodiments, at least one other component can be added in microemulsion.Add all modes of other component to include in the disclosure.
Microemulsion can also comprise that at least one buffering agent is as carbonic acid alkali metal salt, carbonic acid alkali salt, carbonic acid alkali hydrogen slaine, acetate, borate, etc., and their potpourri.In embodiments, described at least one buffering agent will add before microemulsion forms.
The heating for the second time of latex mixture can, at approximately 95 ℃~approximately 145 ℃, more particularly for example be carried out for example approximately 2 hours~approximately 8 hours more particularly approximately 4 hours~approximately 6 hours under the polymerization temperature of approximately 110 ℃~approximately 125 ℃.Heating condition can become according to for example reaction scale and desired result.
The heating for the second time of latex mixture can cause the formation of polymer beads.These polymer beads can combine with at least one amine, with assemble/cohesion polymer particle.In the disclosure, described at least one amine can be water miscible and can comprise any amount of functional group, for example monoamine, diamines and triamine, and as JEFFAMINE T-403, this is a kind of three-functionality-degree alkyl ether amine.Described at least one amine, under the polymkeric substance that comprises at least one alkene class acid anhydrides exists, can react formation each other with the polymer chain of covalence key combination.These polymer chains can be used for again making chain aggregation together subsequently, thereby form larger chain the final particle that forms.
For example, although think in Aquo System, in latex mixture therein can the water of stabilization, be difficult to form acid imide, but have some to form imido precedent in water.See Seijas, J etc., " Microwave enhanced synthesis of bowl-shaped triimideswith C3-symmetry, " Sixth International Electronic Conference onSynthetic Organic Chemistry, on September 30th, 2002.
Described at least one amine can be selected from: diamines, polyoxygenated propane diamine, diethylenetriamine, 2-methyl pentamethylene diamine, hexane diamine, hexamethylene diamine, N-isopropyl-N '-phenyl-phenylenediamine, N-(1,3-dimethylbutyl)-N '-phenyl-phenylenediamine, N, N '-bis-(2-octyl group)-4-phenylenediamine, N, N '-bis-(Isosorbide-5-Nitrae-dimethyl amyl group)-4-phenylenediamine, dihydroxy Tetraphenylbenzidine (DHTBD) etc.The consumption of described at least one amine can become according to the amount of at least one alkene class acid anhydrides.In embodiments, with respect to the amount of toner-particle, the amount of described at least one amine can be approximately 0.5 % by weight~approximately 10 % by weight, for example approximately 1 % by weight~approximately 4 % by weight.
In embodiments, this method provides high monomer to the level of conversion of polymkeric substance or the high degree of polymerization, for example, and approximately 90 % by weight or higher, or approximately 95~100%, for example approximately 98~approximately 100% (conversion percentage refers to whole monomers used in this method).Microemulsion being heated to the second polymerization temperature with after forming polymer beads, can regard gained as latex or emulsion containing the composition of polymer beads.
In embodiments, this method also can comprise isolates polymer beads (may be solid) from liquid phase, and this separation can be passed through classic method, and for example filtration, sedimentation, the dry and similar known method of spraying are realized.
The weight-average molecular weight (Mw) of resulting polymers particle can be for example approximately 3,000~approximately 200,000, more particularly for example approximately 10,000~approximately 150,000.Polymer beads can have narrow distribution, and for example approximately 1.1~approximately 3, more particularly for example approximately 1.1~approximately 2, and for example approximately 1.05~approximately 1.45.The equal diameter of body of polymer beads can be for example about 25nm~approximately 50 μ m, more particularly for example about 100nm~approximately 20 μ m.
Polymer beads optionally with such as known crosslinking chemical or hardening agent as divinylbenzene etc. is cross-linked, carry out in position or in the rear polymerization procedure separating.In polyreaction, can use can not disturb the inventive method and can be products therefrom provides other other optional additives known of strengthening the property, for example colorant, lubricant, release agent or transfer agent, defoamer, antioxidant, etc.
In embodiments, in latex mixture or microemulsion or in any stage of the present invention, all can mix at least one wax.The non-limiting example of wax comprises polypropylene and the tygon that Allied Chemical andPetrolite Corporation sells, wax emulsion, Eastman ChemicalProducts that Michaelman Inc.andthe Daniels Products Company sells, the EPOLENE N-15 that Inc. sells
tM, Sanyo Kasei K.K. sell a kind of lower molecular wt polypropylene VISCOL 550-P
tM, and similar material.The molecular weight Mw of selected commercial polyethylene can be approximately 700~approximately 2500, and commercially available polyacrylic molecular weight can be approximately 4000~approximately 7000.Functionalization wax comprises the AQUA SUPERSLIP 6550 that Micro Powder Inc. for example sells as the example of amine and acid amides
tM, SUPERSLIP6530
tM; Fluoridize wax, the POLYFLUO 190 that for example Micro Powder Inc. sells
tM, POLYFLUO 200
tM, POLYFLUO 523XF
tM, AQUA POLYFLUO411
tM, AQUA POLYSILK 19
tMwith POLYSILK 14
tM; Mixed fluoride amide waxe, the MICROSPERSION 19 for example also being sold by Micro Powder Inc.
tM; Acid imide, ester, quaternary ammonium, carboxylic acid or acrylic polymer emulsions, the JONCRYL 74 for example all being sold by SC JohnsonWax
tM, 89
tM, 130
tM, 537
tMwith 538
tM; Chlorinated polypropylene and tygon that AlliedChemical and Petrolite Corporations sells, and S C Johnson wax.Applicable low-molecular-weight wax is disclosed in United States Patent (USP) 4,659, in 641.
The amount of described at least one wax can be approximately 0.1 % by weight~approximately 15 % by weight that is aggregated monomer total amount, for example approximately 2 % by weight~approximately 10 % by weight.Or described at least one wax can be added in the polymer product of separation of this method.For some toner application, use this component may be very desirable.
Method for producing toner and toner can be prepared by many known methods, in the ZSK53 supplying as Werner Pfleiderer at toner extrusion equipment, the polymer beads that mixes and heat resin or obtain with disclosure method then takes out the method for producing toner and toner forming from equipment.After cooling, can utilize for example Sturtevant comminutor to grind this method for producing toner and toner, object is to make the volume median diameter of toner-particle be less than approximately 25 μ m, for example approximately 6 μ m~approximately 14 μ m, and this diameter is determined with Coulter counter.Other method comprises method well known in the art, as dry, the melt dispersion of spraying, emulsion aggregation and expressing technique.Then, can utilize for example Donaldson Type B classifier to carry out classification to method for producing toner and toner, object is to remove toner particulate, and volume median diameter is less than the toner-particle of approximately 4 μ m.Or toner also can grind with the fluidized bed muller that disposes grading wheel.In embodiments, toner can directly be prepared, thereby abandons grain size segregation and the detachment process of trouble, and method is that the micro emulsion drop before polymerization comprises for example at least one colorant, then isolates the painted toner-particle of gained.
Be suitable for manufacturing emulsion aggregation method existing description in many patents of disclosure toner-particle, for example United States Patent (USP)
5,278,020;5,290,654;5,308,734;5,344,738;5,346,797;5,348,832;5,364,729;
5,366,841;5,370,963;5,376,172;5,403,693;5,418,108;5,405,728;5,482,812;
5,496,676;5,501,935;5,527,658;5,585,215;5,593,807;5,604,076;5,622,806;
5,648,193;5,650,255;5,650,256;5,658,704;5,660,965;5,723,253;5,744,520;
5,763,133;5,766,818;5,747,215;5,804,349;5,827,633;5,853,944;5,840,462;
5,863,698;5,869,215;5,902,710;5,910,387;5,916,725;5,919,595;5,922,501;
5,925,488;5,945,245;5,977,210;6,017,671;6,020,101;6,045,240;6,132,924;
6,143,457; With 6,210,853
In component and method can be selected in embodiment of the present disclosure.
Colorant can be selected from dyestuff and pigment, as United States Patent (USP) 4,788,123; 4,828,956; 4,894,308; 4,948,686; 4,963,455; With 4,965, in 158 disclosed those.That the non-limiting example of pigment comprises is black, blue or green, product red, yellow, and green, orange, palm fibre, purple, indigo plant, red, purple, white and silver color.The non-limiting example of colorant comprises carbon black (for example REGAL
), Flexiverse pigment BFD1121, aniline black byestuffs, aniline blue, magnetic iron ore and painted magnetic iron ore, as Mobay magnetic iron ore MO8029
tM; MO8060
tM; Columbian magnetic iron ore; MAPICO BLACKS
tMwith surface treatment magnetic iron ore; Pfizer magnetic iron ore CB4799
tM, CB5300
tM, CB5600
tM, MCX6369
tM; Bayer magnetic iron ore, BAYFERROX 8600
tM, 8610
tM; Northern pigment magnetic iron ore NP-604
tM, NP-608
tM; Magnox magnetic iron ore TMB-100
tMor TMB-104
tM; Phthalocyanine, 2,9-dimethyl-replacement quinacridine and be designated as the anthraquinone dye of CI 60710, CI Red-1 200 5 in Colour Index; In Colour Index, be designated as two azo dyess of CI26050, CI solvent red 19; In Colour Index, classify four (octadecyl sulfonamide) CuPc, the x-copper phthalocyanine of CI 74160, CI alizarol saphirol as; In Colour Index, be designated as the Anthradanthrene indigo plant of CI 69810; Extraordinary blue X-2137; Diarylide yellow 3,3-dichloro-benzidine N-acetoacetanilide; In Colour Index, be designated as the monoazo pigment of CI 12700, CI solvent yellow 16; In Colour Index, be designated as the nitroaniline sulfonamide of the yellow SE/GLN of Foron, CI disperse yellow 33; 2,5-dimethoxy-4 '-sulfonanilide phenylazo-4 '-chloro-2,5-dimethoxy N-acetoacetanilide; The blue or green pigment dispersion of lasting yellow FGL, pigment yellow 74, B15:3 that Sun Chemicals sells; The pinkish red 81:3 pigment dispersion that Sun Chemicals sells; Huang 180 pigment dispersions that Sun Chemicals sells; Blue or green component etc., and their potpourri.Other industrial pigment that Sun Chemical or Ciba sell with aqueous pigment dispersions includes but not limited to pigment yellow 17, pigment Yellow 14, pigment yellow 93, pigment yellow 74, pigment Violet 23, pigment violet 1, pigment Green 7, pigment orange 36, pigment orange 21, pigment orange 16, paratonere 185, pigment red 122, pigment red 81: 3, pigment blue 15: 3 and pigment Blue-61 and other can reappear the pigment of the maximum Pantone color space.Other applicable colorant includes but not limited to the blue BHD 6000 of Sunsperse carbon black LHD 9303, Sunsperse and the yellow YHD 6001 of Sunsperse that Cinquasia magenta (DuPont), the black A-SF of Levanyl (Miles, Bayer), Sun Chemicals sell, Normandy pinkish red RD-2400, the lasting yellow YE 0305, lasting purple VT 2645, the green XP-111-S of Argyle, Lithol Rubine toner, Royal azarin RD-8192, BG toner GR 0991 and the Ortho orange OR2673 that are all sold by Paul Uhlich, sudan orange G, Tolidine that Aldrich sells are red and E.D.Toluidine is red, all by Matheson, Coleman, Sudan III, Sudan II and SundanIV that Bell sells, scarlet for thermoplastics NSD PS PA that Canada Ugine Kuhlman sells, the red C of Bon that Dominion Color Co. sells, the yellow D0790 of Lumogen that BASF sells, Suco-Gelb L1250, the yellow D 1355 of Suco-, Paliogen purple 5100, Paliogen orange 3040, Paliogen Huang 152, Neopen Huang, the red 3871K of Paliogen, Paliogen red 3340, Paliogen Huang 1560, Paliogen purple 5890, Paliogen indigo plant 6470, Lithol scarlet 4440, Lithol fast scarlet L4300, the scarlet D3700 of Lithol, Lithol fast yellow 0991K, Paliotol Huang 1840, the green L8730 of Heliogen, the blue L6900 of Heliogen, L7202, D6840, D7080, Neopen indigo plant, the blue OS of the Sudan, sudan orange 220 and Fanal powder D4830, the Cinquasia magenta that DuPont sells, the yellow FG1 of Novoperm that Hoechst sells, the Hostaperm powder E all being sold by American Hoechst and PV fast blue B2G01, the blue BCA of Irgalite and Oracet powder RF that Ciba-Geigy sells.Also can use the potpourri of colorant.
Optional colorant can be any desired or effective amount be present in method for producing toner and toner, for example account for approximately 1%~approximately 25% of method for producing toner and toner weight, for example approximately 2%~approximately 15%, for example occupy again approximately 5%~approximately 12% of machine shading composition general assembly (TW).But consumption also can be outside these scopes.
In embodiments, phenylethylene-maleic anhydride resin can be covalently bound at least one colorant and can be generally the reaction product of monomer colorant and phenylethylene-maleic anhydride.Acid anhydrides and styrene, butadiene, methoxy-ethylene base ether, ethene, alpha-olefin, their multipolymer of potpourri etc. are all the suitable examples that can react with monomer colorant of the present disclosure the polymeric material that forms coloured polymer material.
Method for producing toner and toner also optionally comprises charge control additive, as halogenated alkyl pyridine, comprises cetylpyridinium chloride etc., and as United States Patent (USP) 4,298,672 is disclosed; Sulfate and hydrosulfate, comprise as United States Patent (USP) 4,560,635 disclosed distearyl dimethyl methyl ammonium sulfate and as United States Patent (USP) 4,937,157,4,560,635 and the disclosed distearyl dimethyl sulfate of common pending application 07/396, the 497 hydrogen ammonium abandoned; 3,5-di-tert-butyl zinc salicylate compound, as the Bontron E-84 of Japanese Orient Chemical Company sale, or as United States Patent (USP) 4,656,112 disclosed zinc compounds; 3,5-di-tert-butyl salicylic acid aluminium compound, as the Bontron E-88 of Japanese Orient Chemical Company sale, or as United States Patent (USP) 4,845,003 disclosed aluminium compound; As United States Patent (USP) 3,944,493,4,007,293,4,079,014,4,394,430,4,464,452,4,480,021 and 4,560,635 disclosed charge control additive etc., and their potpourri.
The amount of optional charge control additive in method for producing toner and toner can be approximately 0.1 % by weight~approximately 10 % by weight with respect to method for producing toner and toner general assembly (TW), for example approximately 1 % by weight~approximately 5 % by weight.But consumption also can be outside this scope.
Organic shading composition also optionally comprises external surface additive, comprises and helps stream adjuvant, and this class adjuvant is present in toner surface conventionally.The non-limiting example of external surface additive comprise metal oxide as titanium dioxide, tin oxide, they potpourri etc., cataloid as
slaine, aluminium oxide, cerium oxide and their potpourri of slaine and the fatty acid including zinc stearate.United States Patent (USP) 3,590,000 and 3,800,588 have illustrated several above-mentioned adjuvants.In addition, external surface additive can also be United States Patent (USP) 6,004,714,6,190,815 and 6,214, and 507 band coating silicon dioxide.External surface additive can add or be blended on established toner-particle in accumulation process.
Optional external surface additive can be any desired or effective amount exist, for example, with respect to approximately 0.1 % by weight~approximately 5 % by weight of method for producing toner and toner general assembly (TW), for example approximately 0.1 % by weight~approximately 1 % by weight.But consumption also can be beyond this scope.
The disclosure will describe in detail in hereinafter with reference specific embodiments, but should be appreciated that these embodiment to be only intended to explanation and do not plan the disclosure and be limited to material, the conditioned disjunction technological parameter quoted herein.All percentage and umber all refer to weight, except as otherwise noted.
embodiment 1-adds maleic anhydride in latex step
In the styrene/acrylic butyl ester (200ml, conversion ratio~20%, Mn=1900) of bulk polymerization, add maleic anhydride (16g).Heat this potpourri to~50 ℃, until all maleic anhydrides all dissolve.Be added in a kind of aqueous solution (600g water and neopelex (SDBS), 16g) and stirred 5 minutes.Gained potpourri, 500 bar lower piston homogenizing 3 times, is then shifted in the BUCHI reactor of 1 liter.Then reduce pressure (5 times) so that the deoxidation of latex microemulsion with argon gas supercharging.Then be heated 135 ℃.At this temperature, maintain after 1 hour, add ascorbic acid solution (8.5ml, concentration is 0.1g/ml) by pump with the speed of 0.035ml/min.Cooling this reaction after 6 hours, obtains a kind of resin in latex, and particle diameter is~200 μ m, and solids content is 24.9% and Mn=9700 and Mw=23000.
embodiment 2-assembles latex with diamines
To stable free redical polymerization latex (707g, solids content: add 660ml water and pigment (ultramarine-BTD-FX-20,47.8g) 23.48%).At room temperature stirring and in 10 minutes, add a kind of diamines (Jeffamine D-400,6.89g is in 100ml water).By thick gained and suspending liquid in 1 hour, be heated to 55 ℃.Then using NaOH (dense) this suspending liquid that alkalizes is 7.3 to pH value.Then in 2 hours, be heated 95 ℃ and at this temperature, maintain 5 hours.Then by cooling this suspending liquid, filter and wash with water 5 times, be less than 15 μ S/cm until leach the conductivity of thing
2.Gained powder is resuspended in few water of trying one's best and freeze drying, obtains the particle of 130g 13.4 μ m.
embodiment 3-adds maleic anhydride in bulk polymerisation step
Prepare styrene (390ml) and butyl acrylate (110ml) liquid storage, and add TEMPO (3.12g, 0.02mol) and vazo 64 initiating agents (2.0g, 0.0125 mol) in 400ml liquid storage.Under blanket of nitrogen, be heated 135 ℃ (bathe temperature), then dropwise add wherein maleic anhydride (9.8g) to use the solution in the styrene/acrylic butyl ester liquid storage of nitrogen deoxidation at 100ml.Drip and completed in 30 minutes, and then stir 5 minutes, then cooling, gathered (phenylethylene/maleic anhydride-block-styrene/acrylic butyl ester) (Mn=4990, PD=1.23) solution in styrene/acrylic butyl ester monomer.
the preparation of poly-(SMA-block-S/BA) latex of embodiment 4-
In SDBS solution (36g, 1.2 premium on currency), add polymer solution (300ml), styrene (117ml), butyl acrylate (33ml) and the TEMPO (0.6g) of embodiment 3 and stir 5 minutes.Then by this potpourri in approximately 500 bar pressure lower piston homogenizing once, then discharging enters 2 liters of BUCHI reactors.Be heated 135 ℃ (temperature of reactor), in the time that reactor reaches this temperature, dropwise add the ascorbic acid solution (2.4g is in 12ml water) of total amount 8.5ml with the speed of 0.0283ml/min.After keeping 6 hours under temperature of reaction, cooling this reactor, draws off 1401.3g latex, obtains poly-(phenylethylene/maleic anhydride-block-styrene/acrylic butyl ester) (Mn=39168, PD=1.64).
embodiment 5-assembles/condenses latex with diamines as aggregating agent prepared therefrom
In the latex (50ml) of preparing to embodiment 4, add 50ml water and at room temperature stir, regulating pH value to~1.78 simultaneously.Dropwise add wherein 2.89g JeffamineD400 solution (20 % by weight, in water) at 23-25 ℃, then in~1 hour, be slowly heated to the highest 60 ℃.Particle size grows to 6.8 μ m from about 200nm.The pH value of this solution is adjusted to 9.04 with rare NaOH, and then was slowly heated to 95 ℃ in~1.5 hours, and maintain 1.5 hours at this temperature, obtaining particle diameter is the cohesion white particle (Mn=39168) of 6.68 μ m.
Claims (2)
1. a method of preparing toner, comprising:
Heat packs is containing the latex mixture of at least one free radical polymerizable monomer and at least one alkene class acid anhydrides for the first time, with respect at least one free radical polymerizable monomer, the amount of described at least one alkene class acid anhydrides in latex mixture is 0.1 % by weight~20 % by weight;
Heat for the second time this latex mixture to form polymer beads; And
Combine at least one amine and described polymer beads;
Wherein heating-up temperature is higher than heating-up temperature for the first time for the second time, and heating-up temperature is 50 ℃~60 ℃ for the first time, and heating-up temperature is 95 ℃~145 ℃ for the second time.
2. the method for claim 1, is also included in for the first time and with high shear forces, described latex mixture is dispersed in water to form microemulsion after heating.
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-
2004
- 2004-11-17 US US10/989,492 patent/US7615327B2/en not_active Expired - Fee Related
-
2005
- 2005-11-10 CA CA002526745A patent/CA2526745C/en not_active Expired - Fee Related
- 2005-11-14 MX MXPA05012245A patent/MXPA05012245A/en active IP Right Grant
- 2005-11-16 CN CN200510124759.1A patent/CN1776535B/en not_active Expired - Fee Related
- 2005-11-17 JP JP2005332814A patent/JP4819484B2/en not_active Expired - Fee Related
- 2005-11-17 BR BRPI0505302-1A patent/BRPI0505302A/en not_active Application Discontinuation
-
2008
- 2008-04-29 US US12/111,746 patent/US8013074B2/en not_active Expired - Fee Related
- 2008-04-29 US US12/111,697 patent/US7981973B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1062218A (en) * | 1990-11-29 | 1992-06-24 | 佳能公司 | Be used for toner of developing electrostatic image and preparation method thereof |
US6352810B1 (en) * | 2001-02-16 | 2002-03-05 | Xerox Corporation | Toner coagulant processes |
US6500597B1 (en) * | 2001-08-06 | 2002-12-31 | Xerox Corporation | Toner coagulant processes |
Also Published As
Publication number | Publication date |
---|---|
CN1776535A (en) | 2006-05-24 |
US20060105261A1 (en) | 2006-05-18 |
BRPI0505302A (en) | 2006-07-11 |
US7981973B2 (en) | 2011-07-19 |
JP2006146222A (en) | 2006-06-08 |
US7615327B2 (en) | 2009-11-10 |
JP4819484B2 (en) | 2011-11-24 |
CA2526745A1 (en) | 2006-05-17 |
US8013074B2 (en) | 2011-09-06 |
US20080199802A1 (en) | 2008-08-21 |
MXPA05012245A (en) | 2006-05-19 |
US20080213687A1 (en) | 2008-09-04 |
CA2526745C (en) | 2009-06-30 |
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